JP2007211167A - Easily water-dispersible cationized polymer and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an easily water-dispersible cationized polymer which can easily be dispersed in water or an aqueous solvent and can quickly be hydrated or dissolved in water, and to provide a method for producing the same. <P>SOLUTION: This method for producing an easily water-dispersible cationized polymer is characterized by treating a cationized polymer with an aminosilane-based coupling agent. The easily water-dispersible cationized polymer is characterized by being obtained by the production method. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an easily water-dispersible cationized polymer compound and a method for producing the same, and more specifically, an easily water-dispersible cationization that can be easily dispersed in water or an aqueous solvent and can be quickly hydrated and dissolved. The present invention relates to a polymer compound and a method for producing the same.

  Cationic polymer compounds are generally dissolved in water or a mixed solvent containing water (sometimes referred to as “aqueous solvent” in this specification) using hydrophilicity and viscosity determined by the nitrogen content. In general, it is widely used as a conditioning agent for shampoos and body soaps. Examples of such cationized polymer compounds include cationized cellulose, cationized starch, cationized guar gum, cationized locust bean gum, cationized cod gum, cationized collagen, cationized hydrolyzed keratin, and cationized hydrolyzed silk. Etc. are known.

  As described above, these cationized polymer compounds are generally used after being dissolved in water or an aqueous solvent. Therefore, from the standpoint of use, it is important to easily dissolve in water or an aqueous solvent. And it is a very desirable property. Conventionally, commercially available easily dispersible cationized polymer compounds are generally sold in a state of being pulverized into fine particles having an average particle diameter of 100 μm or less so that the dissolution time is shortened. And when actually dissolving in water or an aqueous solvent, this particle size is utilized.

  However, when preparing an aqueous solution or aqueous medium solution using such finely pulverized cationized polymer compound, these finely pulverized cationized polymer compounds are very soluble in water or aqueous solvents. Since it is fast, when it is put into water or an aqueous solvent as it is, only the surface gets wet and dissolves, and sticks to each other to form a lump of cationized polymer compound, so-called “mamako”. Once this “mamako” is formed, the area of contact with water that governs the dissolution rate of the cationized polymer compound is drastically reduced and its dissolution becomes very slow and no longer suitable for industrial processes.

  In order to eliminate the above-mentioned problems, the particle size of the cationized polymer compound is increased to, for example, an average particle size of 500 μm to eliminate the formation of “mamako” and uniformly disperse in water or an aqueous solvent. However, even if it was not possible to substantially prevent the generation of “mamako” and evenly dispersed, the dissolution would be slow due to its large particle size, which is also not practical for use. Not suitable.

  Therefore, as an easily water dispersible cationized polymer compound for preparing an aqueous solution or an aqueous medium solution, it is temporarily insoluble when contacted with water, and therefore is uniformly dispersed in water, and a little. It is desirable to return to easy solubility after a certain period of time, or to develop viscosity by appropriately adding a dissolution initiator, that is, to have excellent dissolution characteristics as a result.

On the other hand, as a technique for imparting desirable properties that are temporarily insoluble when contacted with water to water-soluble cellulose ether, for example, water-soluble cellulose ether is represented by the general formula (R ¹ R ² N—R ³ ). _a Si (Y _b ) X _4-ab (wherein R 1 and R 2 are hydrogen atoms or monovalent organic acids, R 3 is a divalent hydrocarbon group having 3 or more carbon atoms, Y is an alkyl group or an aryl group) , X is an alkoxy group having 1 to 4 carbon atoms, a is a number of 1 or 2, and b is a number of 0, 1, 2 or 3. However, a silane compound represented by 1 ≦ a + b ≦ 4) A technique for processing is known (see Patent Document 1).
However, there is no disclosure of a technique for a cationized polymer compound that is more hydrophilic than cellulose ether and easily forms “Mamako”, and the performance is further improved by specific processing conditions. There is no disclosure.

As a method for obtaining celluloses having desirable characteristics as described above, the most well known and actually used method is to combine a hydroxyl group of cellulose and hemiacetal using glyoxal. This is a method of crosslinking reaction (glyoxal treatment). This glyoxal treatment makes it possible to easily disperse and wet celluloses in water or an aqueous solvent. As a method of such glyoxal treatment, for example, a method of spraying glyoxal as an aqueous solution and drying it on a natural polymer containing a cellulose derivative such as cellulose ether, hydroxypropylmethylcellulose, methylcellulose or a hydroxyl group such as starch is disclosed. (For example, see Patent Documents 2 to 4).
However, there is no disclosure that performance is improved by specific processing conditions. In addition, glyoxal is designated as a mutagenic substance, and there are concerns about safety depending on the use conditions, such as detachment of trace amounts after a long period of time in shampoos and body soaps.

Japanese Patent Publication No. 51-2103 Japanese Examined Patent Publication No.59-45685 Japanese Examined Patent Publication No. 47-1601 Japanese Patent Publication No.42-6664

  An object of the present invention is to solve the conventional problems and achieve the following objects. That is, an object of the present invention is to provide an easily water-dispersible cationized polymer compound that can be easily dispersed in water or an aqueous solvent and can be quickly hydrated and dissolved, and a method for producing the same. .

  As a result of various studies to solve the above-mentioned problems, the present inventors have found that aminosilane coupling is effective for a cationized polymer compound that is highly hydrophilic among water-soluble polymer compounds and easily generates “maco”. Treatment with an agent, preferably under specific conditions, can achieve a temporary insolubilization of the cationized polymer compound in water or an aqueous solvent, resulting in no “maco” formation. It has been found that an easily water-dispersible cationized polymer compound that can be easily dispersed in water or an aqueous solvent and can be quickly hydrated and dissolved can be obtained.

This invention is based on the said knowledge by this inventor, and as a means for solving the said subject, it is as follows. That is,
<1> A method for producing an easily water-dispersible cationized polymer compound, wherein the cationized polymer compound is treated with an aminosilane coupling agent.
<2> The easy water treatment according to <1>, wherein the treatment with the aminosilane coupling agent is performed using 0.1 to 10 parts by mass of the aminosilane coupling agent with respect to 100 parts by mass of the cationized polymer compound. This is a method for producing a dispersible cationized polymer compound.
<3> The treatment with an aminosilane-based coupling agent is performed by reacting the cationized polymer compound with the aminosilane-based coupling agent in the presence of a solvent, and then drying the reaction. <1> to <2> It is a manufacturing method of the easily water dispersible cationized high molecular compound in any one.
<4> The solvent is a mixed solvent of isopropyl alcohol and water, and a mass ratio of the isopropyl alcohol to the water is isopropyl alcohol / water = 70/30 to 95/5. This is a method for producing an easily water dispersible cationized polymer compound.
<5> The method for producing an easily water dispersible cationized polymer compound according to any one of <3> to <4>, wherein the pH during the reaction is 3 to 9.
<6> The method for producing an easily water dispersible cationized polymer compound according to any one of <3> to <5>, wherein a temperature during drying is 60 to 90 ° C.
<7> The method for producing an easily water dispersible cationized polymer compound according to any one of <1> to <6>, wherein the cationized polymer compound is cationized cellulose.
<8> An easily water-dispersible cationized polymer compound obtained by the method for producing an easily water-dispersible cationized polymer compound according to any one of <1> to <7>.
<9> The easily water dispersible cationized polymer compound according to <8> having a pH of 3 to 9.

  According to the present invention, the above-mentioned conventional problems can be solved, the above-mentioned object can be achieved, and the easily water-dispersible cation that can be easily dispersed in water or an aqueous solvent and can be quickly hydrated and dissolved. Polymerized polymer compounds and methods for producing the same can be provided.

  The present invention is described in detail below.

(Method for producing easily water-dispersible cationized polymer compound)
The process for producing an easily water-dispersible cationized polymer compound of the present invention comprises treating the cationized polymer compound with an aminosilane coupling agent, preferably under specific conditions, and if necessary, Including performing other processing.

<Cationized polymer compound>
The cationized polymer compound is not particularly limited and may be appropriately selected depending on the intended purpose. For example, cationized cellulose, cationized starch, cationized guar gum, cationized locust bean gum, cationized tara gum, cation And cationized hydrolyzed keratin and cationized hydrolyzed silk. Among these, cationized cellulose is preferable in terms of industrial utility.

-Degree of cationization-
The degree of cationization of the cationized polymer compound is not particularly limited and may be appropriately selected depending on the intended purpose. It is preferably 0.1 to 5% by mass, more preferably 0.2 to 4% by mass. 0.3 to 3% by mass is particularly preferable.
When the degree of cationization is less than 0.1% by mass, the function as the cationized polymer compound may be lost. When the degree of cationization exceeds 5% by mass, the reactivity with the aminosilane coupling agent is reduced. Sometimes. On the other hand, when the degree of cationization is within the particularly preferable range, the reactivity with the aminosilane coupling agent, and in terms of water dispersibility of the easily water dispersible cationized polymer compound, More advantageous.

-Viscosity-
The viscosity of the cationized polymer compound is not particularly limited and may be appropriately selected depending on the intended purpose. For example, the viscosity of an aqueous solution containing 1% by mass of the cationized polymer compound at 25 ° C. It is preferably 1 to 10,000 mPa · s.

-Shape-
The shape of the cationized polymer compound is not particularly limited and may be appropriately selected depending on the intended purpose. Points such as water dispersibility and solubility of the water-dispersible cationized polymer compound obtained are as follows. It is preferably in the form of a powder, a cake containing water or a solvent, or a slurry dispersed in water or a solvent.
The particle size of the cationized polymer compound when the cationized polymer compound is in a powder form is not particularly limited and may be appropriately selected depending on the intended purpose. Preferably, 50 to 800 μm is more preferable, and 100 to 600 μm is particularly preferable.
When the particle diameter is less than 10 μm or exceeds 1,000 μm, the reactivity may vary and the water dispersibility of the easily water dispersible cationized polymer compound may deteriorate. On the other hand, when the particle diameter is within the particularly preferred range, it is more advantageous in terms of reactivity, and in terms of water dispersibility of the easily water dispersible cationized polymer compound.

<Aminosilane coupling agent>
The aminosilane coupling agent is not particularly limited and may be appropriately selected depending on the intended purpose. For example, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane 3-aminopropyltrimethylethoxysilane, N-2-aminoethyl-3-aminopropyltrimethoxysilane, N-2-aminoethyl-3-aminopropyltriethoxysilane, 3-aminopropyldiethoxysilane, 4-amino Examples include butylmethyldiethoxysilane and N-2-carboethoxyethyl-3-aminopropyltriethoxysilane.
Among these, 3-aminopropyltriethoxysilane, N-2-aminoethyl-3-aminopropyltriethoxysilane, 3-aminopropyltrimethylethoxysilane, 3-aminopropyldiethoxysilane, 4-aminobutylmethyldiethoxy Silane and N-2-carboethoxyethyl-3-aminopropyltriethoxysilane are preferred in that methanol is not liberated when used in shampoos and body soaps.

There is no restriction | limiting in particular as the usage-amount of the said aminosilane type coupling agent, Although it can select suitably according to the objective, 0.1-10 mass parts is with respect to 100 mass parts of said cationized high molecular compounds. Preferably, 0.2-6 mass parts is more preferable, and 0.3-4 mass parts is especially preferable.
When the amount of the aminosilane coupling agent used is less than 0.1 parts by mass with respect to 100 parts by mass of the cationized polymer compound, the inhibitory effect on the production of “mamako” may be weakened. If the amount exceeds mass parts, the production of “mamako” disappears, but the resulting readily water-soluble cationized polymer compound is slowly dissolved in water or an aqueous solvent, and at the same time, the cost is increased, which is not industrially preferable. On the other hand, when the amount of the aminosilane coupling agent used is within the particularly preferable range, there is no generation of “Mamako”, and the resulting easily dispersible cationized polymer compound is dissolved in water or an aqueous solvent. Is advantageous in that it is smoother.

<Processing method>
A method for treating the cationized polymer compound with the aminosilane coupling agent is not particularly limited and may be appropriately selected depending on the intended purpose. For example, the cationized polymer compound and the aminosilane coupling may be selected. A method in which the agent is reacted in the presence of a solvent and then dried; the aminosilane-based coupling agent is sprayed on the dried product of the cationized polymer compound (for example, a particulate product) by spraying, etc. A method of drying again; a method of adding the aminosilane coupling agent to a wet product (for example, slurry) of the cationized polymer compound, and drying using a kneader.
Among these, the method in which the cationized polymer compound and the aminosilane coupling agent are reacted in the presence of a solvent and then dried is preferable from the viewpoint of uniform treatment.

-Preferred treatment method-
Hereinafter, a method (preferred treatment method) in which the cationized polymer compound and the aminosilane coupling agent are reacted in the presence of a solvent and then dried will be described.

--solvent--
The solvent is not particularly limited as long as the aminosilane-based coupling agent can be dissolved and the cationized polymer compound can be dispersed, and can be appropriately selected depending on the purpose. In terms of ease of treatment, those containing a lower alcohol are preferred, and a mixed solvent of a lower alcohol and water is more preferred.
Here, there is no restriction | limiting in particular as said lower alcohol, According to the objective, it can select suitably, For example, isopropyl alcohol, 1-propanol, ethanol, methanol etc. are mentioned. Among these, the easily water-dispersible cationized polymer compound obtained by the above production method can be used for shampoos, body soaps, and the like, and isopropyl alcohol is particularly preferable in terms of ease of removal and securing of yield. .

When the solvent is a mixed solvent of the lower alcohol and water, the mass ratio of the lower alcohol and the water in the solvent is not particularly limited and depends on the type of the cationized polymer compound used. The lower alcohol / water = 70/30 to 95/5 is preferable, and 80/20 to 95/5 is more preferable.
In the solvent, when the water content exceeds 30% by mass, the cationized polymer compound swells excessively during the reaction, and the reaction with the aminosilane coupling agent proceeds to the inside of the cationized polymer compound, The solubility of the resulting easily water dispersible cationized polymer compound may be deteriorated. Moreover, a load is applied to the drying process, which is not preferable. Furthermore, the reactivity with the coupling agent may decrease. Further, if the water content in the solvent is less than 5% by mass, the cationized polymer compound is insufficiently swelled, so that the reaction becomes insufficient, and the resulting easily dispersible cationized polymer compound Dispersibility in water may deteriorate. On the other hand, if the mass ratio of the lower alcohol and the water in the solvent is within the more preferable range, a more appropriate reaction occurs, and the water dispersibility and the solubility in water are improved. This is advantageous in that a molecular compound is obtained.

There is no restriction | limiting in particular as the usage-amount of the said solvent, Although it can select suitably according to the objective, 100-1,000 mass parts is preferable with respect to 100 mass parts of said cationized high molecular compounds, 150- 800 parts by mass is more preferable, and 200 to 600 parts by mass is particularly preferable.
When the amount of the solvent used is less than 100 parts by mass with respect to 100 parts by mass of the cationized polymer compound, the cationized polymer compound is poorly dispersed, and the reaction may not proceed uniformly. When the amount exceeds 1,000 parts by mass, the cationized polymer compound and the aminosilane coupling agent may not sufficiently react. On the other hand, when the amount of the solvent used is within the particularly preferred range, the reactivity is increased, which is advantageous in that the easily water-dispersible cationized polymer compound can be produced more efficiently.

--reaction--
The method of reacting the cationized polymer compound and the aminosilane coupling agent in the presence of the solvent is not particularly limited and may be appropriately selected depending on the purpose. Examples include a method in which the solvent is added to and mixed with the molecular compound, the temperature is raised to a desired reaction temperature, and then the aminosilane coupling agent is added and mixed.

The pH during the reaction is not particularly limited and may be appropriately selected depending on the intended purpose. However, the pH is preferably 3 to 9 and more preferably pH 5 to 7 under the temperature conditions during the reaction. . When the pH is less than 3, the resulting easily water dispersible cationized polymer compound has good water dispersibility, but becomes insoluble and may not dissolve in water. On the other hand, when the pH exceeds 9, the hydration time and dissolution time of the easily water-dispersible cationized polymer compound obtained are shortened, but the dispersibility in water may be deteriorated. On the other hand, when the pH is within the more preferable range, it is advantageous in that the easily water-dispersible cationized polymer compound obtained is superior in water dispersibility, hydration property, and solubility.
The pH can be adjusted by adding inorganic acids such as hydrochloric acid, for example.

There is no restriction | limiting in particular in the temperature at the time of the said reaction, Although it can select suitably according to the objective, 20-80 degreeC is preferable, 25-75 degreeC is more preferable, and 30-70 degreeC is especially preferable.
If the temperature is less than 20 ° C., the reaction does not proceed sufficiently and may cause mamako. If it exceeds 80 ° C., the color tone of the easily water dispersible cationized polymer compound may be deteriorated. . On the other hand, if the temperature is within the particularly preferred range, it is more advantageous in terms of reactivity and color tone.

The time for reacting the cationized polymer compound and the aminosilane coupling agent (reaction time) is not particularly limited and may be appropriately selected depending on the intended purpose, but is preferably 5 to 120 minutes. ~ 100 minutes are more preferable, and 15 to 80 minutes are particularly preferable.
When the reaction time is less than 5 minutes, the reaction may be insufficient and may cause macho, and when it exceeds 120 minutes, the color tone of the easily water dispersible cationized polymer compound may be deteriorated. . On the other hand, when the reaction time is within the particularly preferable range, it is more advantageous in terms of reactivity and color tone.

--Dry--
The drying can be performed, for example, by heating the reaction product obtained after the reaction under reduced pressure or normal pressure to remove the lower alcohol.

  There is no restriction | limiting in particular in the temperature at the time of the said drying, Although it can select suitably according to the objective, 60-90 degreeC is preferable. When the temperature is less than 60 ° C., the reaction between the cationized polymer compound and the aminosilane coupling agent may be insufficient. When the temperature exceeds 90 ° C., the easily water-dispersible cationized polymer obtained. The color tone of the compound may deteriorate.

  It is also preferable to perform liquid removal before the drying. The said liquid removal can be performed by using a centrifugal liquid removal machine using a filter cloth, for example.

  By the production method as described above, among the water-soluble polymer compounds, the cationized polymer compound having high hydrophilicity and easily generating “maco” is easily dispersed in water or an aqueous solvent, and An easily water-dispersible cationized polymer compound (easily water-dispersible cationized polymer compound of the present invention) that can be quickly hydrated and dissolved can be obtained.

(Easily water-dispersible cationic polymer compound)
The easily water-dispersible cationized polymer compound of the present invention is obtained by the method for producing the easily water-dispersible cationized polymer compound, and can be easily dispersed in water or an aqueous solvent, and can be quickly hydrated and dissolved. It has the characteristic that it is.
Here, the properties (water dispersibility, hydration time, dissolution time, color tone, etc.) of the water-dispersible cationized polymer compound can be confirmed by, for example, the evaluation method described in the examples described later. it can.

-PH-
The pH of the water-dispersible cationized polymer compound is not particularly limited and may be appropriately selected depending on the intended purpose. For example, 1% by mass of the water-dispersible cationized polymer compound is included. About aqueous solution, it is preferable that it is pH 3-9 under 25 degreeC conditions, and it is more preferable that it is pH 5-7. When the pH is less than 3, the dispersibility in water is good, but it becomes insoluble and may not dissolve in water. On the other hand, when the pH exceeds 9, the hydration time and dissolution time are shortened, but the dispersibility in water may be deteriorated. On the other hand, when the pH is in the more preferable range, it is advantageous in that it is superior in water dispersibility, hydration property, and solubility.
The pH can be adjusted, for example, by adjusting the pH during the reaction of the cationized polymer compound and the aminosilane coupling agent in the method for producing the easily water dispersible cationized polymer compound.

-Shape-
The shape of the easily water dispersible cationized polymer compound is not particularly limited and may be appropriately selected depending on the intended purpose. However, in terms of water dispersibility and solubility, a powder form is preferable. The particle diameter of the easily water-dispersible cationized polymer compound when the easily water-dispersible cationized polymer compound is in a powder form is not particularly limited and can be appropriately selected according to the purpose. 10-1,000 micrometers is preferable, 30-800 micrometers is more preferable, and 50-600 micrometers is especially preferable.
When the particle diameter is less than 10 μm, dust may be easily generated during use, and when it exceeds 1,000 μm, it may take a long time to dissolve. On the other hand, when the particle diameter is within the particularly preferable range, it is more advantageous in terms of solubility and handling properties.
In order to obtain a powdery water-dispersible cationized polymer compound having a desired particle size as described above, for example, a cationized polymer compound used in the method for producing the water-dispersible cationized polymer compound The particle diameter of the powder may be selected as appropriate.

  The easily water-dispersible cationized polymer compound of the present invention can be easily dispersed in water or an aqueous solvent without forming so-called “mamako”, and can be quickly hydrated and dissolved. It is useful in a wide range of applications such as shampoos, body soap conditioning agents, hair cosmetics, basic cosmetics, makeup cosmetics, aromatic cosmetics, tanning cosmetics, sunscreen cosmetics, nail cosmetics, and bath cosmetics. Furthermore, since it is excellent in safety as compared with a conventional glyoxal-treated product, it is particularly useful as a conditioning agent for shampoos and body soaps.

  EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated concretely, this invention is not limited to these Examples.

  (A) Water dispersibility, (b) hydration time, (c) dissolution of the water-dispersible cationized polymer compound obtained in each example and the cationized polymer compound obtained in each comparative example Evaluation of time and (d) color tone was performed as follows, respectively.

(A) Water dispersibility 106-425 μm water-dispersible cationized polymer compound obtained by adding 50 g of ion-exchanged water to a 100 mL beaker and fractionating with a sieve. (Same as in (a) to (d))] 2 g of powder was added. The dispersibility of the powder was visually evaluated.
〔Evaluation criteria〕
A: All powders are dispersed in water.
○: More than half of the powder is dispersed in water.
X: The powder is hardly or not dispersed at all (aggregates on the water surface to form “Mamako”).

(B) Hydration time 100 g of ion-exchanged water at 25 ° C. was added to a 100 mL beaker and set in a three-one motor (manufactured by HEIDOH). A stirring blade having a diameter of 40 mm was used, and the lower part of the blade was set to be 2 cm above the lower part of the beaker. The stirring rotation speed was 400 rpm (however, when a cationized polymer compound other than cationized cellulose was used, it was 800 rpm). While stirring, 2 g of a 106-425 μm easily water-dispersible cationized polymer compound obtained by fractionation with a sieve was added and dissolved. The time from when the water-dispersible cationized polymer compound was added to when the viscosity of the solution increased until the liquid level became horizontal was measured.

(C) Dissolution time In the same manner as in (b), the time from when the easily water-dispersible cationized polymer compound was introduced to when the easily water-dispersible cationized polymer compound was completely dissolved was measured. The amount of the water-dispersible cationized polymer compound used for the measurement was also 2 g as in (b).

(D) Color tone About the 106-425 micrometer easily water-dispersible cationized polymer compound powder obtained by fractionating with a sieve, the color tone was evaluated by visual comparison with the corresponding untreated product.
Here, the untreated product is any one of cationized cellulose, cationized starch, and cationized guar gum shown in Comparative Examples 3 to 5 described later. Depending on the type of polymer compound of the easily water dispersible cationized polymer compound powder to be evaluated, an untreated product of the same polymer compound was used for comparison.
〔Evaluation criteria〕
A: Less colored than untreated product.
○: The degree of coloring is the same as the untreated product.
X: There exists coloring (it is inferior) compared with an untreated product.

(Production Example 1)
Production of cationized cellulose Hydroxyethyl cellulose (manufactured by Sumitomo Seika: LF-15, 2% by weight aqueous solution viscosity (25 ° C.): 1,200 mPa · s) 30 g (100 parts by mass) isopropyl alcohol / water (mass ratio) ) = 85/15 300 g (1,000 parts by mass) of a mixed solvent, and 4.5 g (15 parts by mass) of a 25% by mass aqueous sodium hydroxide solution were added and mixed. Thereafter, the mixture was stirred and mixed for 30 minutes, and 150 g (500 parts by mass) of the supernatant of the mixed solvent was extracted. Then, the temperature was raised to 50 ° C., 15 g (50 parts by mass) of glycidyltrimethylammonium chloride (manufactured by Sakamoto Yakuhin: SY-GTA80, effective amount: 73% aqueous solution) was added as a cationizing agent and reacted for 3 hours.
Then, 10 mass% hydrochloric acid IPA solution was added to adjust to pH 6, and a cationized cellulose slurry was obtained. And it spin-dehydrated and passed through drying (70-80 degreeC), and obtained the cationized cellulose.

(Production Example 2)
Production of cationized starch Low cationized starch (manufactured by Nippon Corn Starch: TAPLLINK-3, degree of cationization: 0.3% by mass, effective content: 87%) per 30 g (100 parts by mass) isopropyl alcohol / water = 80 144 g (480 parts by mass) of the mixed solvent to be / 20, and 4.5 g (15 parts by mass) of a 15% by mass aqueous sodium hydroxide solution were further added and mixed. Then, the temperature was raised to 55 ° C., and 9.6 g (32 parts by mass) of glycidyltrimethylammonium chloride (Sakamoto Yakuhin: SY-GTA80, effective content: 73% aqueous solution) was added as a cationizing agent and reacted for 3 hours. . Then, 10 mass% hydrochloric acid IPA solution was added to adjust to pH 6 to obtain a cationized starch slurry. And it spin-dehydrated and passed through drying (70-80 degreeC), and obtained the cationized starch.

(Production Example 3)
Production of Cationized Guam Gum Isopropyl alcohol / water with respect to 30 g (100 parts by mass) of guar gum (manufactured by Mishoku: Maplogur CSAA, effective content: 85%, 1% by mass viscosity (25 ° C.): 3,500 mPa · s) 150 g (500 parts by mass) of the mixed solvent to be 80/20 and 6 g (20 parts by mass) of a 15% by mass aqueous sodium hydroxide solution were added and mixed. Then, the temperature was raised to 55 ° C., and 13.5 g (45 parts by mass) of glycidyltrimethylammonium chloride (manufactured by Sakamoto Pharmaceutical: SY-GTA80, effective amount: 73% aqueous solution) as a cationizing agent was added and reacted for 3 hours. . Then, 10 mass% hydrochloric acid IPA solution was added to adjust to pH 6 to obtain a cationized guar gum slurry. And it spin-dehydrated and passed through drying (70-80 degreeC), and obtained cationized guar gum.

Example 1
The cationized cellulose obtained in Production Example 1 (degree of cationization: 1.8% by mass, 2% by mass aqueous solution viscosity (25 ° C.): 350 mPa · s) 30 g (100 parts by mass) isopropyl alcohol / water (mass) 150 g (500 parts by mass) of a mixed solvent with a ratio of 85/15 was added and mixed, and the temperature was raised to 50 ° C. Thereafter, as an aminosilane coupling agent, 0.6 g (2 parts by mass) of 3-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBE-903, effective content: 100%) is added and mixed, and reacted at pH 6 for 30 minutes. I let you. Then, the desiccated cake was dried at 80 ° C. to obtain a target water-dispersible cationized cellulose powder (easy water-dispersible cationized polymer compound).
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was very good and it quickly hydrated and dissolved. The color tone was also good.
Table 1 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 2)
The same easy water as in Example 1, except that the same cationized cellulose as in Example 1 was used, and a mixed solvent in which isopropyl alcohol / water (mass ratio) = 75/25 was used and treatment was performed at pH 8. A dispersible cationized cellulose powder was obtained.
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 1 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 3)
The objective easily water-dispersible cationization was carried out in the same manner as in Example 1, except that the same cationized cellulose as in Example 1 was used and a mixed solvent in which isopropyl alcohol / water (mass ratio) = 95/5 was used. Cellulose powder was obtained.
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 1 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

Example 4
The same cationized cellulose as in Example 1 was used, N-2-aminoethyl-3-aminopropyltriethoxysilane (effective content: 100%) was used instead of 3-aminopropyltriethoxysilane, and isopropyl alcohol / water. (Mass ratio) = 80/20 was used, and the target water-dispersible cationized cellulose powder was obtained in the same manner as in Example 1 except that the mixture was treated at pH 10.
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 1 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 5)
Example except that the same cationized cellulose as in Example 1 was used, a mixed solvent in which isopropyl alcohol / water (mass ratio) = 80/20 was used, the treatment was performed at pH 2, and the drying temperature was 100 ° C. In the same manner as in Example 1, a desired easily water dispersible cationized cellulose powder was obtained.
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 1 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 6)
Example 1 except that the same cationized cellulose as in Example 1 was used, a mixed solvent in which isopropyl alcohol / water (mass ratio) = 65/35 was used, the treatment was performed at pH 10, and the drying temperature was 100 ° C. In the same manner as described above, a desired water-dispersible cationized cellulose powder was obtained.
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 1 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 7)
Using the same cationized cellulose as in Example 1, using 0.06 g (0.2 parts by mass) of 3-aminopropyltriethoxysilane (effective content: 100%), isopropyl alcohol / water (mass ratio) = 80 / The target easily water-dispersible cationized cellulose was obtained in the same manner as in Example 1 except that the mixed solvent of 20 was used.
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was somewhat worse than that of Example 1, but there was no problem and it quickly hydrated and dissolved. The color tone was also good.
Table 2 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 8)
Using the same cationized cellulose as in Example 1, 1.5 g (5 parts by mass) of 3-aminopropyltriethoxysilane (effective part: 100%), isopropyl alcohol / water (mass ratio) = 80/20 The target water-dispersible cationized cellulose was obtained in the same manner as in Example 1 except that the mixed solvent was used.
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. Dispersibility was good and hydrated quickly. However, the dissolution time was somewhat longer than in Examples 1-7. The color tone was good.
Table 2 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

Example 9
The cationized starch obtained in Production Example 2 (degree of cationization: 1.5 mass%, 1 mass% aqueous solution viscosity (25 ° C.): 3,000 mPa · s), 30 g (100 mass parts), isopropyl alcohol / water 150 g (500 parts by mass) of a mixed solvent with (mass ratio) = 80/20 was added and mixed, and the temperature was raised to 50 ° C. Thereafter, 0.6 g (2 parts by mass) of 3-aminopropyltrimethoxysilane was added and mixed, and reacted at pH 6 for 30 minutes. Thereafter, the lysed powder was dried at 80 ° C. to obtain a target easily water-dispersible cationized starch (easy water-dispersible cationized polymer compound).
The obtained easily water-dispersible cationized starch was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 2 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 10)
The objective easily water-dispersible cationization was carried out in the same manner as in Example 9 except that the same cationized starch as in Example 9 was used and a mixed solvent in which isopropyl alcohol / water (mass ratio) = 95/5 was used. Starch was obtained.
The obtained easily water-dispersible cationized starch was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 2 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 11)
Cationized guar gum obtained in Production Example 3 (degree of cationization: 1.8% by mass, 1% by mass aqueous solution viscosity (25 ° C.): 2,700 mPa · s) 30 g (100 parts by mass) isopropyl alcohol / water 150 g (500 parts by mass) of a mixed solvent with (mass ratio) = 80/20 was added and mixed, and the temperature was raised to 50 ° C. Thereafter, 0.6 g (2 parts by mass) of 3-aminopropyltrimethoxysilane was added and mixed, and reacted at pH 6 for 30 minutes. Thereafter, the lysed powder was dried at 80 ° C. to obtain the desired easily water dispersible cationized guar gum (easy water dispersible cationized polymer compound).
The obtained easily water dispersible cationized guar gum was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 2 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 12)
The same easily water-dispersible cationization as in Example 11 except that the same cationized guar gum as in Example 11 was used and a mixed solvent in which isopropyl alcohol / water (mass ratio) = 95/5 was used. Guam gum was obtained.
The obtained easily water dispersible cationized guar gum was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 2 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Comparative Example 1)
Using the same cationized cellulose as in Example 1, instead of 3-aminopropyltriethoxysilane, treatment was performed with methyltriethoxysilane, which is a non-aminosilane coupling agent, and isopropyl alcohol / water (mass ratio) = 80. A cationized cellulose was obtained in the same manner as in Example 1 except that a mixed solvent of / 20 was used.
The obtained cationized cellulose was evaluated by each evaluation item. Although the color tone was good, mamako was formed and was not dispersed in water, and the hydration time and dissolution time could not be measured.
Table 3 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Comparative Example 2)
Using the same cationized cellulose as in Example 1, instead of 3-aminopropyltriethoxysilane, treatment was performed with 3-glycidoxypropyltrimethoxysilane (effective content: 100%), which is a non-aminosilane coupling agent. The cationized cellulose was obtained in the same manner as in Example 1 except that a mixed solvent in which isopropyl alcohol / water (mass ratio) = 80/20 was used.
The obtained cationized cellulose was evaluated by each evaluation item. Although the color tone was good, mamako was formed and was not dispersed in water, and the hydration time and dissolution time could not be measured.
Table 3 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Comparative Example 3)
The same cationized cellulose as in Example 1 was used, and evaluation was performed on each evaluation item without any treatment. Although the color tone was good, mamako was formed and was not dispersed in water, and the hydration time and dissolution time could not be measured.
Table 3 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Comparative Example 4)
The same cationized starch as in Example 9 was used, and the evaluation was performed on each evaluation item without any treatment. Although the color tone was good, mamako was formed and was not dispersed in water, and the hydration time and dissolution time could not be measured.
Table 3 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Comparative Example 5)
The same cationized guar gum as in Example 11 was used, and evaluation was performed on each evaluation item without any treatment. Although the color tone was good, mamako was formed and was not dispersed in water, and the hydration time and dissolution time could not be measured.
Table 3 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

(Example 13)
In Example 13, a cationized cellulose in a slurry state was used to produce an easily water dispersible cationized cellulose.
First, a cationized cellulose slurry was prepared as follows.
Hydroxyethyl cellulose (manufactured by Sumitomo Seika: LF-15, 2% by weight aqueous solution viscosity (25 ° C.): 1,200 mPa · s) 30 g (100 parts by mass) isopropyl alcohol / water (mass ratio) = 85/15 300 g (1,000 parts by mass) of the mixed solvent, and 4.5 g (15 parts by mass) of a 25% by mass aqueous sodium hydroxide solution were added and mixed. Thereafter, the mixture was stirred and mixed for 30 minutes, and 210 g (700 parts by mass) of the supernatant of the mixed solvent was extracted. Then, the temperature is raised to 50 ° C., and 15 g (50 parts by mass) of glycidyltrimethylammonium chloride (Sakamoto Yakuhin: SY-GTA80, effective content: 73% aqueous solution) is added as a cationizing agent and reacted at 50 ° C. for 3 hours. It was. Then, 10 mass% hydrochloric acid IPA solution was added to adjust to pH 6, and a cationized cellulose slurry was obtained.
Next, the obtained cationized cellulose slurry was subjected to silane treatment in a slurry state as follows.
0.6 g (2 parts by mass) of 3-aminopropyltriethoxysilane was added to the obtained cationized cellulose slurry, neutralized again to pH 6, raised from 50 ° C. to 60 ° C., and reacted for 1 hour. I let you. Thereafter, centrifugal dehydration was performed, and the resultant was dried at 80 ° C. under reduced pressure for 5 hours to obtain a target easily water dispersible cationized cellulose (easy water dispersible cationized polymer compound).
The obtained easily water-dispersible cationized cellulose was evaluated by each evaluation item. The dispersibility was good and it quickly hydrated and dissolved. The color tone was also good.
Table 4 shows reaction conditions, product pH (1% by mass aqueous solution, 25 ° C.), and evaluation results.

  From the results of Tables 1 to 4, according to the method for producing an easily water-dispersible cationized polymer compound of the present invention, the dispersibility in water is good and the hydration time and dissolution time are excellent. It was found that a water dispersible cationized polymer compound was obtained.

The easily water-dispersible cationized polymer compound of the present invention can be easily dispersed in water or an aqueous solvent without forming so-called “mamako”, and can be quickly hydrated and dissolved. It is useful in a wide range of applications such as shampoos, body soap conditioning agents, hair cosmetics, basic cosmetics, makeup cosmetics, aromatic cosmetics, tanning cosmetics, sunscreen cosmetics, nail cosmetics, and bath cosmetics. Furthermore, since it is excellent in safety as compared with a conventional glyoxal-treated product, it is particularly useful as a conditioning agent for shampoos and body soaps.

Claims (9)

  A method for producing an easily water-dispersible cationized polymer compound, comprising treating a cationized polymer compound with an aminosilane coupling agent.   The easily water-dispersible cation according to claim 1, wherein the treatment with the aminosilane coupling agent is performed using 0.1 to 10 parts by mass of the aminosilane coupling agent with respect to 100 parts by mass of the cationized polymer compound. Process for producing a polymer compound.   The treatment with an aminosilane coupling agent is performed by reacting a cationized polymer compound and an aminosilane coupling agent in the presence of a solvent, followed by drying. A method for producing an easily water-dispersible cationized polymer compound.   The easy water dispersion according to claim 3, wherein the solvent is a mixed solvent of isopropyl alcohol and water, and the mass ratio of the isopropyl alcohol and the water is isopropyl alcohol / water = 70/30 to 95/5. Of producing a cationic cationic polymer compound.   The method for producing an easily water dispersible cationized polymer compound according to any one of claims 3 to 4, wherein the pH during the reaction is 3 to 9.   The method for producing an easily water dispersible cationized polymer compound according to any one of claims 3 to 5, wherein a temperature during drying is 60 to 90 ° C.   The method for producing an easily water-dispersible cationized polymer compound according to any one of claims 1 to 6, wherein the cationized polymer compound is cationized cellulose.   An easily water-dispersible cationized polymer compound obtained by the method for producing an easily water-dispersible cationized polymer compound according to any one of claims 1 to 7.   The easily water-dispersible cationized polymer compound according to claim 8, having a pH of 3 to 9.